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Hydrochloric Acid → N-(2,6-diethylphenyl)-N'-(4-phenylcyclohexyl)urea

HRID 37292
Notes
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Reaction equation

HRID 37292 reaction equation
[C:1]1([CH:7]2[CH2:12][CH2:11][CH:10]([NH2:13])[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:14]([C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([CH2:22][CH3:23])[C:17]=1[N:24]=[C:25]=[O:26])[CH3:15].N1C=CC=CC=1.Cl>ClCCl>[CH2:14]([C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([CH2:22][CH3:23])[C:17]=1[NH:24][C:25]([NH:13][CH:10]1[CH2:9][CH2:8][CH:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH2:12][CH2:11]1)=[O:26])[CH3:15]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 298974-PhenylcyclohexylamineHCID 51531832,6-Diethylphenyl isocyanate

Product 1

HCID 19935160N-(2,6-diethylphenyl)-N'-(4-phenylcyclohexyl)urea

Reagents, catalysts & solvents 1

HCID 6344Dichloromethane
Solvent

Procedure

To a solution of 1 g of 4-phenylcyclohexylamine in 10 ml of dichloromethane was added 2,6-diethylphenylisocyanate dropwise in the presence of pyridine and the mixture was stirred for 2 hours at room temperature. To the resultant mixture was added 30 ml of diluted hydrochloric acid and the solution was extracted with chloroform. The extract was washed with water, aqueous sodium hydrogencarbonate solution and saturated brine, and then dried over magnesium sulfate. The solvent was distilled away and the residue was crystallized from methanol to give 0.4 g of N-(2,6-diethylphenyl)-N'-(4-phenylcyclohexyl)urea, melting at 247°-249° C.

Workup

  1. extractionthe solution was extracted with chloroform
  2. washThe extract was washed with water, aqueous sodium hydrogencarbonate solution and saturated brine
  3. dry with materialdried over magnesium sulfate
  4. distillationThe solvent was distilled away
  5. customthe residue was crystallized from methanol

Sources & evidence

ORD record
ord-c23ebd5f61fc415c985902eea7eba4c6
Source dataset
uspto-grants-1995_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05420164

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes